Ring Enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-Deoxy-L-Allonojirimicina

Dondoni, A.; Richichi, Barbara; Marra, A.; Perrone, D.

doi:10.1055/s-2004-829566

Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions afforded the corresponding R-protected pyrrolidines and 2-deoxy-piperidines in different ratios depending on the stereochemistry of the starting pyrrolidine and the nature of the acid R-OH. A mechanistic scheme is proposed involving the formation of an aziridinium ion as an intermediate.

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Titolo:	Ring Enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-Deoxy-L-Allonojirimicina
Autori di Ateneo:	A. DONDONI RICHICHI, BARBARA A. MARRA D. PERRONE mostra contributor esterni nascondi contributor esterni
Autori:	A. DONDONI; RICHICHI, BARBARA; A. MARRA; D. PERRONE
Data di pubblicazione:	2004
Rivista:	SYNLETT
Volume:	10
Pagina iniziale:	1711
Pagina finale:	1714
Abstract:	Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions afforded the corresponding R-protected pyrrolidines and 2-deoxy-piperidines in different ratios depending on the stereochemistry of the starting pyrrolidine and the nature of the acid R-OH. A mechanistic scheme is proposed involving the formation of an aziridinium ion as an intermediate.
Handle:	http://hdl.handle.net/2158/340334
Appare nelle tipologie:	1a - Articolo su rivista

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